Azo dyes



Patented Nov. 7, 1939 UNITED STATES PATENT OFFICE AZO DYES

No Drawing. Application July 3, 193 Serial No. 151,962

6 Claims.

A. This invention relates to azo dyes for cellulose, by which term is meant not only the usual celluloses but also regenerated celluloses.

B. Demand has arisen in the art for developed brown and red colors for cellulose which have qualities of fastness to washing which are not possessed by colors of similar shade. at the present time. Accordingly we have sought to produce such dyes.

in C. It is an object of the invention, consequently, to produce'new developed brown and red dyes of outstanding fastness to washing when applied to cellulose and which have in addition the other qualities of fastness which are essential to a commercial product.

D. The objects of the invention are accomplished, generally speaking, by dyeing cellulose from aqueous medium with a compound represented by the formula:

5. in which X is one of a group consisting of hydrogen, and Aryl-N=N, Y is one or more of the group consisting of hydrogen, halogen, alkyl, alkoxy, carboxy, and sulfonic acid, and the end Aryl has a single nucleus from the class consisting of benzene, naphthalene, diphenyl, phenylmethyl-pyrazolone, and Aryl of interior components has a single nucleus from'the class consisting of benzene, naphthalene, and diphenyl, diazotizing the compound on the fiber and cou- 45 pling it to beta naphthol, diphenyl, acetoacetanilide, and phenyl-alkyl-pyrazolone. In the preferred form of the invention the phenyl-alkylpyrazolone will be l-phenyl-3-methyl-5-pyrazolone and the diphenyl will be meta-tolylene diamine. In a still more preferred form of the invention the coupling component is betanaphthol.

E. 'I'he method of producing the products on the fiber is illustrated in the following examples which are given for the purpose of illustration and not for limitation.

Example I Five parts of cotton piece goods is dyed in the usual manner, known to those skilled in the art, with ten hundredths parts of Z-naphthylamine- 6:8-disulfonic acid meta-toluidine Z-aminobenzidine. The dyed fabric is rinsed in cold water and put in 200 parts of water at C. Add threetenths parts of sodium nitrite and four-tenths parts of sulfuric acid. Stir 15 minutes. Rinse with cold water. Dissolve one tenth part of beta naphthol in 200 parts of water and one twentieth part of caustic soda. Stir the solution rapidly while-adding the above rinsed piece goods. Stir 15 minutes. Rinse in cold water and dry. The dyeing is a reddish brown shade. The formula of the dye is:

N803 S N N l O HO NaOzS N:

F. In the following table are given other examples produced by a similar method showing the shade produced on cellulose.

Example Diazo component Coupling component ggfogg cel- 2 Z-naphthy1amine-4z8-disulfonie acid metatoluidinemetatolui- Beta naphthol Maroon brown.

dine 2-amino-benzidine.

3 do Do.

4 do-.. Acetoacet-anilide Yellowbrown.

5 do l-phenyl-3-methyl-5-pyrazolone Do.

6 2-2;.mino benzidine benzidine l-(sulfopl1enyl)-3-methyl-5-pyrazo- Beta naphthol Orange brown.

one.

7 2-an1ino benzidine benzidine (alkalme) Z-amino-8-hydr0xy-naphtha- .do Red brown.

lene-B-sulfonic acid. a

8 2-an1 i1o-benzidine -benzidine alpha-naphthylamine-G-sulionic do Maroon brown.

aci

9 2-amino-benzidinebenzidine (alkalme) l-amino-S-hydroxy-naphtha- Reddish brown.

lene-3z6-disullonic acid. Y a

10 2-naphthylamine-6:S-disulionic acidmeta toluidine.meta-toluido Bordeaux.

dine 2-amino-benzidine.

11 (Hydrolyzed,acetyl-paraphenylene-dian1ine alpha-naphthylamine-6- do Maroon brown.

sulIonic-acid- 2-amino-benzidine.

l2 Z-naghthylamine-fi:8-uisulfonicacid metatoluidinc- 2-amino-bendo. Bed brown.

Zl me.

G. In the foregoing table the arrows inean'c'oupled by the diazo reaction. p q

H. These dyes have outstanding fastness t washing and fastness to light, heat, etc., equal to that of competing products.

I. A method of manufacturing the diazo components of this case is described in Jordan etal., Serial No. 151,961 filed July 3, 1937.

J. As many apparently widely different embodiments of this invention may be made without departing from the spirit'and scope thereof,'it is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.

We claim:

1. A compound represented by the formula: 1

in which Y is one or more of the group-consisting of hydrogen, halogen, alkyl, alkoxy, carboxy, and sulfonic acid, the end Aryl has a single nucleus from the class consisting of benzene, naphthalene, diphenyl, and phenyl-alkyl-pyrazolone,

NaOaiS Na 03S pli'n g.component having a single nucleus from the class consistingof benzene, naphthalene, di-

phenyl, phenyl-alkyl-pyrazolone, and acetoacetanilide, and the compound has at least one water- 'solubilizing group.

The compound represented by the formula:

I 1 HO N=N 4. The compound represented by the formula:

=N N=N- -N=N slow 5. The compound of claim 4 in which each beta naphthol coupling component is replaced by 1- phenyl-3-methyl-5-pyrazolone.

6. The process which comprises diazotizing a 25 compound represented by the formula:

NH: Y

, from the class consisting of benzene, naphthalene,

and diphenyl, and coupling it to one of a group of azo dyestufi coupling components from the class consisting of benzene, naphthalene, diphenyl, phenyl-alkyl-pyrazolone, and. acetoacetanilide, the dyestuff in its completed form having at least one water-solubilizing group.

HENRY JORDAN. SWANIE S. ROSSANDER. 

